1. Field of the Invention
The present invention relates to a process for producing amines useful as intermediate or the like for medicines, agricultural chemicals or the like.
2. Description of the Related Art
Previously, for a process for producing of an optically active intermediate used for medicines, agricultural chemicals or the like, for example, methods using a metal compound have been known. However, the method has a problem that must dispose of the metal compound used.
In order to solve such problem, Non-patent Literature 1 (J. Org. Chem., Vol. 68, No. 25, 9624 (2003)) and Non-patent Literature 2 (J. Am. Chem. Soc., Vol. 24, No. 9, 1842 (2002)) report a method of reacting a carbonyl compound and an imine using L-proline or a derivative thereof in place of a metal compound.
However, the method described in the Non-patent Literature 1 has a problem that must perform reduction reaction with a reducing agent such as sodium borohydride and the like after the reaction using L-proline, and the method described in the Non-patent Literature 2 has a problem that must use a large amount (more than a catalytic amount) of the catalyst of L-proline.
Non-patent Literature 3 (THE NINTH INTERNATIONAL KYOTO CONFERENCE OF NEW ASPECTS OF ORGANIC CHEMISTRY, Program, Abstracts, List of Participants, p 116, (2003)) describes a process for producing an optically active N-protected β-amino acid by reacting trimethylsilyl vinyl ether and an N-(2-hydroxyphenyl)imine with a chiral phosphoric acid derivative.
However, the method described in the Non-patent Literature 3 has a problem that a substrate to be reacted with an imine must be trimethylsilylated into trimethylsilyl vinyl ether.
In addition, Non-patent Literature 4 (The ninth International Kyoto Conference on New Aspects of Organic Chemistry, 2003, Nov., 10-14 (poster presentation was held on November 11th) Abstracts, p. 116, No. PA004) discloses a phorphoric acid derivative of the formula (1), but only shows use in a reaction of obtaining α-aminophosphonic acid from an imine and a phosphorous acid diisopropyl ester.